1516
S. Stavber et al.
PAPER
13C NMR (CDCl3): = 143.65 (ArC), 139.75 (ArC), 138.25 (ArC),
129.49 (ArC), 127.78 (ArC), 101.16 (C-I), 27.79 (CH2), 20.25
(CH3), 15.49 (CH3).
MS: m/z (%) = 246 ([M]+, 100), 231 (76), 119 (35), 104 (26), 91
(23), 77 (12).
1H NMR (CDCl3): = 1.18 (s, 3 H, CH3), 1.20 (s, 3 H, CH3), 2.99
(s, 3 H, CH3), 3.28 (hept, J = 6.8 Hz, 1 H, CH), 7.68 (s, 1 H, H-Ar).
13C NMR (CDCl3): = 153.43 (ArC), 144.09 (ArC), 136.89 (ArC),
117.81 (C-I), 116.67 (C-I), 100.30 (C-I), 43.00 (CH3), 40.59 (CH),
23.73 (CH3).
HRMS: m/z Calcd for C9H11I: 245.9906. Found: 245.9911.
MS: m/z (%) = 512 ([M]+, 100), 497 (53), 128 (65), 91 (86).
Anal. Calcd for C9H11I: C, 43.92; H, 4.51. Found: C, 43.36; H 4.65.
HRMS: m/z Calcd for C10H11I3: 511.7995. Found: 511.8010.
Anal. Calcd for C10H11I3: C, 23.46; H, 2.17. Found: C, 23.60; H,
2.17.
1-Ethyl-2,5-diiodo-4-methylbenzene (3b)
White crystals; mp 36.5–38 °C; yield: 73%.
IR (KBr): 2940, 1450, 1430, 1030, 875 cm–1.
5-(tert-Butyl)-1,3-diiodo-2-methylbenzene (5b)
Yellow oil; yield: 80%.
IR (Neat): 2963, 2909, 1522, 1443, 1379, 1258, 1036, 872 cm–1.
1H NMR (CDCl3): = 1.26 (s, 9 H, t-C4H9), 2.70 (s, 3 H, CH3), 7.80
(s, 2 H, H-Ar).
13C NMR (CDCl3): = 152.55 (ArC), 139.90 (ArC), 136.93 (ArC4,
ArC6), 99.29 (C1-I, C3-I), 34.43 (2-CH3), 34.03 [C(CH3)3], 31.07
[C(CH3)3].
1H NMR (CDCl3): = 1.16 (t, J = 7.5 Hz, 3 H, CH3), 2.33 (s, 3 H,
CH3), 2.63 (q, J = 7.5 Hz, 2 H, CH2), 7.61 (s, 1 H, H-Ar), 7.65 (s, 1
H, H-Ar).
13C NMR (CDCl3): = 145.81 (ArC), 140.75 (ArC), 139.69 (ArC),
138.21 (ArC), 101.02 (C-I), 99.87 (C-I), 33.11 (CH2), 26.87 (CH3),
14.47 (CH3).
MS: m/z (%) = 372 ([M]+, 90), 357 (52), 245 (44), 230 (30), 118
(85), 117 (100), 103 (37), 91 (56), 77 (43).
MS: m/z (%) = 400 ([M]+, 55), 385 (100), 258 (15), 128 (52), 127
HRMS: m/z Calcd for C9H10I2: 371.8872. Found: 371.8887.
(26), 91 (21), 57 (50).
Anal. Calcd for C9H10I2: C, 29.06; H, 2.71. Found: C, 28.75; H,
2.50.
HRMS: m/z Calcd for C11H14I2: 399.9185. Found: 399.9199.
Anal. Calcd for C11H14I2: C, 33.02; H, 3.53. Found: C, 32.73; H,
3.32.
2-Iodo-4-isopropyl-1-methylbenzene (4a)
Colourless oil; yield: 72%.
IR (Neat): 2961, 1487, 1455, 1395, 1029, 819 cm–1.
1,4-Diiodo-2,5-diisopropylbenzene (6b)
White crystals; mp 85.5–86.5 °C; yield: 81%
1H NMR (CDCl3): = 1.19 (s, 3 H, CH3), 1.21 (s, 3 H, CH3), 2.38
(s, 3 H, CH3), 2.79 (hept, J = 6.8 Hz, 1 H, CH), 7.07–7.15 (m, 2 H,
H-Ar), 7.66 (s, 1 H, H-Ar).
13C NMR (CDCl3): = 148.33 (ArC), 138.53 (ArC), 136.93 (ArC),
129.35 (ArC), 126.33 (ArC), 101.26 (C-I), 33.23 (CH3), 27.52
(CH), 23.90 (CH3).
IR (KBr): 2923, 1460, 1340, 1300, 1225, 1180, 1000, 868 cm–1.
1H NMR (CDCl3): = 1.19 (s, 6 H, CH3), 1.21 (s, 6 H, CH3), 3.05
(hept, J = 6.8 Hz, 2 H, CH), 7.60 (s, 2 H, H-Ar).
13C NMR (CDCl3): = 149.91 (ArC2, ArC5), 136.60 (ArC3, ArC6),
101.42 (C1-I, C4-I), 37.48 (CH), 22.98 (CH3).
MS: m/z (%) = 414 ([M]+, 100), 399 (95), 272 (18), 257 (15), 145
(21), 128 (18), 115 (20).
MS: m/z (%) = 260 ([M]+, 75), 245 (100), 133 (18), 118 (76), 117
(28), 91 (22).
HRMS: m/z Calcd for C12H16I2: 413.9342. Found: 413.9357.
HRMS: m/z Calcd for C10H13I: 260.0062. Found: 260.0070.
Anal. Calcd for C12H16I2: C, 34.81; H, 3.89. Found: C, 34.51; H,
3.66.
Anal. Calcd for C10H13I: C, 46.17; H, 5.04. Found: C, 45.99; H,
5.26.
1-Iodo-2,4-diisopropylbenzene (7a)
Yellow oil; yield: 89%.
IR (Neat): 2962, 1460, 1390, 1360, 1040, 995, 877, 805 cm–1.
1H NMR (CDCl3): = 1.22 (s, 6 H, CH3), 1.24 (s, 6 H, CH3), 2.85
(hept, J = 6.8 Hz, 1 H, CH), 3.17 (hept, J = 6.8 Hz, 1 H, CH), 6.76
(d, J = 8 Hz, 1 H, H-Ar), 7.08 (s, 1 H, H-Ar), 7.71 (d, J = 8 Hz, 1 H,
H-Ar).
13C NMR (CDCl3): = 150.06 (ArC), 149.43 (ArC), 139.26 (ArC),
125.83 (ArC), 124.33 (ArC), 97.50 (C-I), 37.93 (CH), 33.91 (CH),
23.91 (CH3), 23.12 (CH3).
1,4-Diiodo-2-isopropyl-5-methylbenzene (4b)
Yellow oil; yield: 77%.
IR (Neat): 2962, 1454, 1375, 1315, 1060, 1020, 877 cm–1.
1H NMR (CDCl3): = 1.18 (s, 3 H, CH3), 1.22 (s, 3 H, CH3), 2.33
(s, 3 H, CH3), 3.06 (hept, J = 6.8 Hz, 1 H, CH), 7.59 (s, 1 H, H-Ar),
7.66 (s, 1 H, H-Ar).
13C NMR (CDCl3): = 149.75 (ArC), 140.85 (ArC), 139.79 (ArC),
135.99 (ArC), 101.43 (C-I), 100.55 (C-I), 37.36 (CH), 26.90 (CH3),
23.00 (CH3).
MS: m/z (%) = 386 ([M]+, 100), 371 (82), 244 (58), 119 (34), 117
(34), 91 (22).
MS: m/z (%) = 288 ([M]+, 63), 273 (100), 131 (30), 91 (18).
HRMS: m/z Calcd for C12H17I: 288.0375. Found: 288.0377.
HRMS: m/z Calcd for C10H12I2: 385.9029. Found: 385.9041.
Anal. Calcd for C12H16I2: C, 50.01; H, 5.95. Found: C, 49.81; H,
6.25.
Anal. Calcd for C10H12I2: C, 31.12; H, 3.13. Found: C, 31.17; H,
3.17.
1,5-Diiodo-2,4-diisopropylbenzene (7b)
White crystals; mp 49–53 °C; yield: 71%.
IR (KBr): 2963, 1450, 1377, 1348, 1040, 1000, 874 cm–1.
1H NMR (CDCl3): = 1.20 (s, 6 H, CH3), 1.22 (s, 6 H, CH3), 3.11
1,3,4-Triiodo-5-isopropyl-2-methylbenzene (4c)
Yellow oil; yield: 70%.
IR (Neat): 2961, 2924, 1460, 1408, 1306, 1073, 1039, 996, 875
cm–1.
(hept, J = 6.8 Hz, 2 H, CH), 7.09 (s, 1 H, H-Ar), 8.23 (s, 1 H, H-Ar).
Synthesis 2002, No. 11, 1513–1518 ISSN 0039-7881 © Thieme Stuttgart · New York